KR20140118926A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

Provided in the present invention are a heterocyclic compound and an organic light emitting device comprising the same. Provided in the present invention is a heterocyclic compound presented by following chemical formula 1. The heterocyclic compound according to embodiments of the present invention has a proper energy level, and has excellent electrochemical stability and thermal stability. Therefore, an organic light emitting device including the compound provides high efficiency and/or high driving stability.

Description

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present invention relates to heterocyclic compounds and organic light emitting devices containing them.

This specification claims the benefit of Korean Patent Application No. 10-2013-0034206, filed on March 29, 2013, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation, is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

Therefore, there is a need in the art to develop new organic materials.

J. Chem. Soc., 1950, 1065-1067

It is an object of the present invention to provide a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

The present invention provides a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In formula (1)

m and n are each an integer of 0 to 5,

o is an integer from 0 to 2,

p is an integer of 0 to 4,

When n, m, o and p are 2 or more, R ', R, R2 and R3 are the same as or different from each other,

R1 to R3, R and R 'are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocyclic ring,

At least one of R1 to R3 is any one of the following formulas,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,

R10 to R14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted imine group, a substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocyclic ring.

In addition, in one embodiment of the present specification, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound do.

Heterocyclic compounds according to embodiments of the present disclosure have suitable energy levels and are excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

1 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is provided.

In one embodiment of the present disclosure, at least one of R 1 to R 3 is any one of the following formulas:

R10 to R13 and L1 are as defined above.

또는

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

or

Quot; refers to a moiety bonded to another substituent or bond.

The above substituent functions as an n-type substituent. In the case of a bipolar host comprising a compound having an n-type substituent and a p-type substituent, the hole and / or electron mobility is excellent and the device has an excellent effect.

In one embodiment of the present invention, benzene rings are condensed at positions 4 and 5 of the indole group. When the benzene ring is condensed at positions 4 and 5 of the indole group, the benzene ring is positioned in the opposite direction (para position) to the N atom of the relatively weak indole group upon electron entry, There is an excellent effect of stability. Accordingly, the organic light emitting device including the heterocyclic compound according to one embodiment of the present specification is excellent in stability.

In one embodiment of the present specification, R1 is any one of the following formulas.

R10 to R13 and L1 are as defined above. When the substituent is substituted at the R 1 position, the substituent functions as an n-type substituent. In the case of a bipolar host comprising a compound having an n-type substituent and a p-type substituent, the hole and / or electron mobility is excellent and the device has an excellent effect.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; Thiol group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Carbazole group; An aryl group; A fluorenyl group; Arylalkyl groups; An arylalkenyl group; And a heterocyclic group containing at least one of N, O and S atoms, or does not have any substituent (s).

The substituents may be substituted or unsubstituted with an additional substituent.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same or different from each other.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the imine group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be mono- or di-substituted by nitrogen of the amide group with hydrogen, a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 2 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, N-octyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And the like. However, the present invention is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom, which may be monocyclic or polycyclic, and may be an aliphatic or aromatic ring.

The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group, but the present invention is not limited thereto.

In the present specification, the alkyl group in the alkylthio group and the alkylsulfoxy group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.

In the present specification, adjacent groups mean respective substituents in which R, R ', R2 and R3 are adjacent to each other when m, n, o and p are 2 or more.

In the present specification, adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocyclic ring, the adjacent substituents are bonded to each other to form a 5- to 8-membered hydrocarbon ring or a heterocyclic ring, . ≪ / RTI >

The hydrocarbon ring includes an aliphatic ring, an aromatic ring, or a condensed ring of aliphatic and aromatic rings, and may be monocyclic or polycyclic.

The heterocyclic ring includes an aliphatic ring, an aromatic ring, or a condensed ring of aliphatic and aromatic groups, and may be monocyclic or polycyclic.

In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied, except that these are two groups each.

In one embodiment of the present disclosure, R is hydrogen.

In one embodiment of the present disclosure, R 'is hydrogen.

In one embodiment of the present disclosure, R 2 is hydrogen.

In one embodiment of the present disclosure, R3 is hydrogen.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다.In one embodiment of the present disclosure, R1 is

to be.

이다. In one embodiment of the present disclosure, R1 is

to be.

이다.In one embodiment of the present disclosure, R1 is

to be.

이다.
In one embodiment of the present disclosure, R1 is

to be.

In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L1 is a substituted or unsubstituted phenylene group.

In one embodiment of the present invention, L1 is a phenylene group.

또는

이다. In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group, and the phenylene group is

or

to be.

In one embodiment of the present specification, L1 is a substituted or unsubstituted biphenylene group.

In one embodiment of the present invention, L1 is a biphenylene group.

In one embodiment of the present specification, L1 is a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L1 is a naphthylene group.

In one embodiment of the present specification, R10 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R10 is a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, R10 is a phenyl group.

In one embodiment of the present specification, R10 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R10 is a naphthyl group.

In one embodiment of the present disclosure, R10 is hydrogen.

In one embodiment of the present specification, R11 is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, R11 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R11 is a phenyl group.

In one embodiment of the present invention, R11 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R11 is a naphthyl group.

In one embodiment of the present disclosure, R11 is hydrogen.

In one embodiment of the present specification, R12 is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, R12 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R12 is a phenyl group.

In one embodiment of the present specification, R12 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, R12 is a naphthyl group.

In one embodiment of the present specification, R12 is hydrogen.

 In one embodiment of the present specification, R13 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R13 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R13 is a phenyl group.

In one embodiment of the present specification, R13 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, R13 is a naphthyl group.

In one embodiment of the present specification, R13 is hydrogen.

In one embodiment of the present specification, R14 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R14 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R14 is a phenyl group.

In one embodiment of the present invention, R14 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R14 is a naphthyl group.

In one embodiment of the present specification, R14 is hydrogen.

In one embodiment of the present specification, R10 to R14 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 4-1 to 4-33.

The compound of formula (1) may be prepared based on the preparation examples described below. The heterocyclic compounds represented by the general formula (1) as well as the heterocyclic compounds represented by the general formulas (4-1) to (4-33) can be prepared by a general method known in the art such as a condensation reaction and a Suzuki coupling reaction .

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And an organic layer formed of one or more layers including a light emitting layer provided between the first electrode and the second electrode,

Wherein at least one of the organic material layers comprises the heterocyclic compound.

In one embodiment of the present disclosure, a layer including a hole injecting layer, a hole transporting layer, or hole injecting and hole transporting at the same time, and including the hole injecting layer, the hole transporting layer, .

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, And the above heterocyclic compound.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound.

In one embodiment of the present invention, the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant.

When the heterocyclic compound according to one embodiment of the present invention is used as a host, the hole and / or electron mobility is improved as a bipolar host, thereby providing a high voltage, high efficiency and / or long life organic light emitting device.

In one embodiment of the present invention, the phosphorescent dopant compound is represented by the following general formula (7).

(7)

In formula (7)

M1 is Ir or Os,

L10, L11 and L12 are the same or different and independently of each other are any one of the following structures,

d ', f', g ', h', j, j ', and q', p, q, q ', r, s, t, u', v ', w', x ', a, b', c ' k is an integer of 0 to 4,

each of r ', s', t', u, v, w, x, y, y 'and e'

b, e, h, i, k 'and 1 are integers of 0 to 3,

c and g 'each represent an integer of 0 to 2,

f 'is an integer of 0 to 5,

z is an integer of 0 to 8,

R110 to R165 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; Alkyl silyl group, a substituted or unsubstituted C ₂ ~ _10; A substituted or unsubstituted C ₆ ~ ₃₀ arylsilyl group; A substituted or unsubstituted alkyl group of C _1-10; A substituted or unsubstituted C ₂ ~ C ₁₀ alkenyl; Alkoxy group, a substituted or unsubstituted C ₁ ~ ₁₀ ring; A substituted or unsubstituted C ₆ -C ₂₀ aryl group; And a substituted or unsubstituted C ₅ to C ₂₀ heterocyclic group, or adjacent groups form a condensed ring of a monocyclic or polycyclic aliphatic, aromatic aliphatic hetero or heteroaromatic ring.

In one embodiment of the present invention, the phosphorescent dopant compound represented by Formula 7 is any one of the following compounds.

In one embodiment of the present disclosure, the content of the dopant relative to the total weight of the photoactive layer is 7 wt% to 15 wt%. In the above-mentioned range, the lifetime of the device can be excellent along with the efficiency of the appropriate device. If the content of the dopant exceeds 15 wt%, the lifetime of the device is increased, but the efficiency of the device is deteriorated.

In one embodiment of the present invention, the organic material layer further includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to the present invention is illustrated in FIGS.

1 shows an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 shows a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

The organic light-emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the heterocyclic compound.

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the heterocyclic compound may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In one embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

The substrate can be selected in consideration of optical properties and physical properties as required. For example, the substrate is preferably transparent. The substrate may be of a rigid material, but may also be of a flexible material such as plastic.

In addition to glass and quartz, the material of the substrate may be selected from the group consisting of polyethyleneterephthalate (PET), polyethylene naphthalate (PEN), polypropylene (PP), polyimide (PI), polycarbonate (PC), polystyrene (PS), polyoxymethylene (acrylonitrile butadiene styrene copolymer), TAC (triacetyl cellulose) and PAR (polyarylate), but are not limited thereto.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. The hole injecting material preferably has a highest occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic material, phthalocyanine derivative, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, Perylene-based organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

In one embodiment of the present invention, the organic light emitting diode may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

In one embodiment of the present invention, the heterocyclic compound may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The heterocyclic compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< Example >

< Manufacturing example  1> 1 of  Synthesis of compounds

[Formula 4-1A]

[Formula 4-1]

Preparation of 4-1A

After dissolving 2-hydroxy-1,2-diphenylethanone (21.2 g, 100 mmol) and 2-naphthylamine (14.3 g, 100 mmol) in ethanol (300 ml), ZnCl ₂ (0.14 g, And the mixture was stirred for 24 hours while boiling. Water was added to terminate the reaction, and the resulting solid was filtered. The residue was dissolved again in chloroform, and MgSO ₄ was added to remove water. After filtration, the volume of the solvent was reduced by distillation, and hexane was added thereto to obtain a white solid (29g, yield 90%). MS: [M + H] &lt; ⁺ &gt; = 320

The 4- 1 of  Produce

4-1A (32.0 g, 100 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine ( 26.7 g, 100 mmol) was dissolved in toluene -t- butoxy sodium (after boil put 14.4 g, 150 mmol) Pd ( P (t-Bu) ₃ side 0.1 equiv) ₂ catalyst into the mixture was stirred for 3 hours. After the solution was cooled to room temperature, the filtrate was stirred, and the resulting solid was filtered. The resulting solid was recrystallized from chloroform and ethanol to obtain the compound of Formula 4-1 (41 g, yield 78%). MS: [M + H] &lt; ⁺ &gt; = 551

< Manufacturing example  2> 2 of  Synthesis of compounds

[Formula 4-2]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-diphenylpyridine (4-2) was obtained in the same manner as in the production of the compound of the formula (4-1), except that 2-chloro-4,6-diphenylpyrimidine was used. MS: [M + H] &lt; + &gt; = 550

< Manufacturing example  3> 3 of  Synthesis of compounds

[Formula 4-3]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 4-chloro-2,6-diphenylpyridine 4-3 was obtained in the same manner as in the preparation of the compound of formula (4-1), except that 4-chloro-2,6-diphenylpyrimidine was used. MS: [M + H] &lt; ⁺ &gt; = 550

< Manufacturing example  4> 4 of  Synthesis of compounds

[Formula 4-4]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 4-chloro-2,6-diphenylpyridine 4-4 was obtained in the same manner as in the preparation of the compound of formula (4-1), except that 4-chloro-2,6-diphenylpyrimidine was used. MS: [M + H] &lt; ⁺ &gt; = 550

< Manufacturing example  5> 6 of  Synthesis of compounds

[Formula 4-6]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-dinaphthyl 4-1, except that 2-chloro-4,6- (1-dinaphthyl) -1,3,5-triazine was used instead of 2-chloro-4- 4-6. MS: [M + H] &lt; ⁺ &gt; = 651

< Manufacturing example  6> 7's  Synthesis of compounds

[Formula 4-7]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl- 4-1, except that 2-chloro-4,6- (1-dinaphthyl) -1,5-pyrimidine was used instead of 2-chloro-4- 4-7. MS: [M + H] &lt; ⁺ &gt; = 650

< Manufacturing example  7> 8 of  Synthesis of compounds

[Formula 4-8]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl- 4-1, except that 2-chloro-4,6- (1-dinaphthyl) -1,3-pyrimidine was used instead of 2-chloro-4- 4-8. MS: [M + H] &lt; ⁺ &gt; = 650

< Manufacturing example  8> Ten  Synthesis of compounds

[Formula 4-10]

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl- (4-10) was obtained in the same manner as in the production of the compound of the formula (4-1) except that 2-chloro-4,6- (1-dinaphthyl) -1-pyridine was used instead of 2- . MS: [M + H] &lt; ⁺ &gt; = 649

< Manufacturing example  9> Eleven  Synthesis of compounds

[Formula 4-11A]

[Formula 4-11]

Preparation of Formula 4-11A

2-chloro-4,6-diphenyl-1,3,5-triazine (26.7 g, 100 mmol) and 4-chlorophenyl after the acid (4-chlorophenyl boronic acid) ( 15.6 g, 100 mmol) was dissolved in tetrahydrofuran (THF), and stirred under boiling was added to the calcium carbonate aqueous solution, Pd (PPh _{3) 4} catalyst into 0.01 eq. After stirring for 12 hours, the mixture was cooled to room temperature, and the organic layer was separated. The organic layer was recrystallized from chloroform and ethanol to obtain 4-11A white solid (31 g, yield 88%). MS: [M + H] &lt; ⁺ &gt; = 344

The 4- Eleven  Produce

Except that 4-11A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. (4-11) was obtained in the same manner as in the production method of &lt; RTI ID = 0.0 &gt; MS: [M + H] &lt; ⁺ &gt; = 628

< Manufacturing example  10> Thirteen  Synthesis of compounds

[Formula 4-13A]

[Formula 4-13]

Preparation of Formula 4-13A

4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine 4-13A was obtained in the same manner as in the production of the compound of the formula 4-11A. MS: [M + H] &lt; + &gt; = 343

Preparation of Formula 4-13

4-13A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 &gt; was obtained in the same manner as in the production method of &quot; -1 &quot;. MS: [M + H] &lt; ⁺ &gt; = 626

< Manufacturing example  11> Fifteen  Synthesis of compounds

[Chemical Formula 4-15A]

[Chemical Formula 4-15]

Preparation of Formula 4-15A

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in place of 2-chloro-4,6-diphenyl- 4-15A was obtained in the same manner as in the preparation of the compound of the formula 4-11A, except that 2-chloro-4,6-diphenylpyridine was used instead of 2-chloro-4,6-diphenylpyridine. MS: [M + H] &lt; ⁺ &gt; = 342

Preparation of formulas 4-15

Except that 4-15A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 &gt; was obtained in the same manner as in the production method of &lt; 1 &gt; MS: [M + H] &lt; ⁺ &gt; = 625

< Manufacturing example  12> 16  Synthesis of compounds

[Formula 4-16A]

[Chemical Formula 4-16]

Preparation of Formula 4-16A

4-11A, except that 3-chloro-phenyl boronic acid was used in place of 4-chloro-phenyl boronic acid. 4-16A was obtained. MS: [M + H] &lt; ⁺ &gt; = 344

Preparation of 4-16

4-16A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 &lt; / RTI &gt; MS: [M + H] &lt; ⁺ &gt; = 627

< Manufacturing example  13> 17  Synthesis of compounds

[Formula 4-17A]

[Formula 4-17]

Preparation of Formula 4-17A

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, 2-chloro-4,6-diphenylpyridine 4-17A was obtained in the same manner as in the preparation of the compound of the formula 4-16A, except that 2-chloro-4,6-diphenylpyrimidine was used. MS: [M + H] &lt; ⁺ &gt; = 344

Preparation of 4-17

Except that 4-17A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 &lt; / RTI &gt; MS: [M + H] &lt; ⁺ &gt; = 626

< Manufacturing example  14> Of 26  Synthesis of compounds

[Chemical Formula 4-26A]

[Chemical Formula 4-26]

Preparation of Formula 4-26A

Instead of 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl- 4-ylamine was used instead of 2-chloro-4,6- (1-dinaphthyl) -1,3,5-triazine (4-26A). MS: [M + H] &lt; ⁺ &gt; = 444

Preparation of Formula 4-26

Except that 4-26A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- -1 &gt; was obtained in the same manner as in the production method of &lt; 1 &gt; MS: [M + H] &lt; ⁺ &gt; = 727

< Manufacturing example  15> Synthesis of the compound of the following formula 4-31

[Formula 4-31A]

[Formula 4-31]

Preparation of Formula 4-31A

Dibromobenzene (20 g, 85 mmol) was dissolved in tetrahydrofuran (100 ml) and then cooled to -78 ° C. n-BuLi (2.5 M, 37 ml, 93 mmol) was slowly added dropwise and stirred for 30 minutes. Chlorodiphenylphosphine (17 g, 76 mmol) was slowly added dropwise, stirred for 3 hours, then warmed to room temperature, water (100 ml) was added, and the mixture was extracted with tetrahydrofuran. The organic layer was concentrated and recrystallized from hexane to obtain a white solid. The residue was dissolved in trichloromethane (200 ml), and hydrogen peroxide solution (20 ml) was added thereto, followed by stirring for 12 hours. Magnesium sulfate (MgSO ₄ ) was added and stirred to remove water, followed by filtration, concentration and recrystallization from hexane to obtain 4-31A (18 g, yield 85%). MS: [M + H] &lt; ⁺ &gt; = 357

Preparation of 4-31

Except that 4-31A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6- -1-propan-1-one. MS: [M + H] &lt; ⁺ &gt; = 727

< Manufacturing example  16> Synthesis of Compound of Formula 4-32

[Formula 4-32A]

[Formula 4-32]

Preparation of 4-32A

4-32A was obtained in the same manner as in the production of 4-31A except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene. MS: [M + H] &lt; ⁺ &gt; = 407

Preparation of 4-32

Except that 4-32A was used in place of 2-chloro-4,6-diphenyl-1,3,5-triazine. -1 &gt; was obtained in the same manner as in the production method of &lt; 1 &gt; MS: [M + H] &lt; ⁺ &gt; = 646

< Example  1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing dispersant and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and distilled water was secondarily filtered using a filter manufactured by Millipore Co. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of solvent of isopropyl alcohol, acetone, and methanol, and dried.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. NPB (400 Å), which is a material for transporting holes, was vacuum deposited thereon. Then, the compound of Formula 4-1 synthesized in Preparation Example 1 and the compound D1 as a dopant were vacuum deposited to a thickness of 300 Å. E1 and LiQ were then thermally vacuum deposited with (200 A) electron injection and transport layer. Lithium quinolate (LiQ) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.

CBP was used as a comparative example of the light emitting layer host.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of lithium quinolate was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.

[Hexaazatriphenylene] [NPB]

[CBP] [D1]

[B1]

< Example  2>

The same experiment was conducted except that the light emitting layer host in Example 1 was used in place of the compound of Formula 4-1.

< Example  3>

The same experiment was carried out except that the light emitting layer host in Example 1 was used in place of the compound of Formula 4-1.

< Example  4>

The same experiment was conducted except that the light emitting layer host in Example 1 was used in place of the compound of Formula 4-1.

< Comparative Example  1>

The same experiment was carried out except that CBP was used in place of the compound 1-1 in the light emitting layer host in Example 1.

Table 1 shows the results of an experiment on an organic light emitting device manufactured by using each compound as a light emitting layer host as in the above embodiment.

Experimental example (5 mA / cm ² ) Host material Voltage (V) Efficiency (cd / A) Comparative Example 1 CBP 4.19 19.03 Example 1 4-1 4.01 21.00 Example 2 4-16 3.96 23.29 Example 3 4-26 4.55 24.21 Example 4 4-31 6.23 14.50

1: substrate
2: anode
3: Hole injection layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode

Claims (11)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]

In formula (1)
m and n are each an integer of 0 to 5,
o is an integer from 0 to 2,
p is an integer of 0 to 4,
When n, m, o and p are 2 or more, R ', R, R2 and R3 are the same as or different from each other,
R1 to R3, R and R 'are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocyclic ring,
At least one of R1 to R3 is any one of the following formulas,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group containing at least one of N, O and S atoms,
R10 to R14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted imine group, a substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms, or adjacent groups are bonded to each other to form a hydrocarbon ring or a heterocyclic ring. The method according to claim 1,
Wherein R &lt; 1 &gt; is any one of the following formulas:

R10 to R14 and L1 are the same as defined in the above formula (1). The method according to claim 1,
L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group. The method according to claim 1,
R10 to R14 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (4-1) to (4-33).

A first electrode; A second electrode facing the first electrode; And at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers contains the heterocyclic compound according to any one of claims 1 to 5. The method of claim 6,
Wherein the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transport and electron injection,
Wherein the electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and injects electrons comprises the heterocyclic compound. The method of claim 6,
Wherein the light emitting layer comprises the heterocyclic compound. The method of claim 6,
Wherein the light emitting layer contains the heterocyclic compound as a host and a phosphorescent dopant compound as a dopant. The method of claim 6,
Wherein the organic material layer includes a hole transporting layer or a hole injecting layer,
Wherein the hole transport layer or the hole injection layer comprises the heterocyclic compound. The method of claim 6,
Wherein the organic material layer is a hole injection layer, a hole transport layer. An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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